β-cellobiosyl fluoride | 7584-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-cellobiosyl fluoride
• 英文别名: O⁴-β-D-glucopyranosyl-β-D-glucopyranosyl fluoride；O⁴-β-D-Glucopyranosyl-β-D-glucopyranosylfluorid；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-Fluoro-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 7584-85-2
• 化学式: C₁₂H₂₁FO₁₀
• 分子量: 344.291
• InChiKey: MPJMJSVSVMGORJ-QRZGKKJRSA-N

物化性质

• 沸点：
  639.0±55.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-cellobiosyl fluoride 以 acetate buffer 、 溶剂黄146 为溶剂， 生成 Cellobiose
  参考文献：
  名称：

  Simultaneous detection of different glycosidase activities by 19F NMR spectroscopy

  摘要：

  A fast method for the simultaneous detection of different glycosidolytic activities in commercially available enzyme preparations and crude culture filtrates was found in using, as substrate, a mixture of different glycosyl fluorides and F-19 NMR spectroscopy as a screening technique. Accompanying studies regarding the hydrolytic stability of these fluorides in various buffer systems, as well as conditions of their long-term storage, were carried out. A simple procedure for the preparation of beta-D-mannopyranosyl fluoride in gram quantities is given. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00060-4
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 sodium methylate 作用下， 生成 β-cellobiosyl fluoride
  参考文献：
  名称：

  Micheel et al., Chemische Berichte, 1955, vol. 88, p. 475,479

  摘要：

  DOI：

文献信息

• A Single Point Mutation Alters the Transglycosylation/Hydrolysis Partition, Significantly Enhancing the Synthetic Capability of an <i>endo</i>-Glycoceramidase
  作者：Julien Durand、Xevi Biarnés、Laurie Watterlot、Cyrielle Bonzom、Vinciane Borsenberger、Antoni Planas、Sophie Bozonnet、Michael J. O’Donohue、Régis Fauré

  DOI：10.1021/acscatal.6b02159

  日期：2016.12.2

  The mutation of D311 to tyrosine in endo-glycoceramidase II from Rhodococcus sp. and the use of a poorly recognized substrate, 2-chloro-4-nitrophenyl β-cellobioside, have provided appropriate conditions for the efficient synthesis of alkyl β-cellobioside derivatives. The mutant D311Y was characterized by a lowered KM value for the hydrolysis of 2-chloro-4-nitrophenyl β-cellobioside and increased transglycosylation

  Rhodococcus sp。的内切糖酰胺酶II中D311突变为酪氨酸。以及使用公认的底物2-氯-4-硝基苯基β-纤维二糖苷为有效合成烷基β-纤维二糖苷衍生物提供了适当的条件。突变体D311Y的特征是K M降低当使用脂肪族1,3-二醇或带有δ-羟基酮功能的醇作为受体时，2-氯-4-硝基苯基β-纤维二糖苷的水解度增加，反式糖基化增加。进一步的分析表明，该突变体催化的反应中的转糖基化/水解率完全相反，并且弱的二次水解被推迟，从而为高转糖基化产率（68％至93％）奠定了基础。总体而言，结果证实，通过结合不稳定的过渡态和增加对受体分子的识别，可以实现糖苷水解酶中转糖基化的增强。
• Stereochemical course of the action of the cellobioside hydrolases I and II of Trichoderma reesei
  作者：Jonathan K. C. Knowles、P�ivi Lentovaara、Martin Murray、Michael L. Sinnott

  DOI：10.1039/c39880001401

  日期：——

  With β-cellobiosyl fluoride as substrate, CBHI gives β-cellobiopyranose as the first product, whereas CBHI gives α-cellobiopyranose (CBH = cellobioside hydrolase).

  以β-纤维二磺酰氟为底物，CBHI产生β-纤维二吡喃糖作为第一产物，而CBHI产生α-纤维二吡喃糖（CBH =纤维二糖苷水解酶）。
• KNOWLES, JONATHAN K. C.;LENTOVAARA, PAIVI;MURRAY, MARTIN;SINNOTT, MICHAEL+, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 21, C. 1401-1402
  作者：KNOWLES, JONATHAN K. C.、LENTOVAARA, PAIVI、MURRAY, MARTIN、SINNOTT, MICHAEL+

  DOI：——

  日期：——
• Micheel et al., Chemische Berichte, 1955, vol. 88, p. 475,479
  作者：Micheel et al.

  DOI：——

  日期：——
• Simultaneous detection of different glycosidase activities by 19F NMR spectroscopy
  作者：Martin Albert、Werner Repetschnigg、Jörg Ortner、Joseph Gomes、Bernhard J. Paul、Carina Illaszewicz、Hansjörg Weber、Walter Steiner、Karl Dax

  DOI：10.1016/s0008-6215(00)00060-4

  日期：2000.8

  A fast method for the simultaneous detection of different glycosidolytic activities in commercially available enzyme preparations and crude culture filtrates was found in using, as substrate, a mixture of different glycosyl fluorides and F-19 NMR spectroscopy as a screening technique. Accompanying studies regarding the hydrolytic stability of these fluorides in various buffer systems, as well as conditions of their long-term storage, were carried out. A simple procedure for the preparation of beta-D-mannopyranosyl fluoride in gram quantities is given. (C) 2000 Elsevier Science Ltd. All rights reserved.